61473-76-5Relevant academic research and scientific papers
Stereoselective preparation of mono- and bis-derivatives of pentacyclo[6.3.0.02,6.03,10.05,9] undecane (D 3-trishomocubane)
Mishura, Anastasiia M.,Sklyarova, Anna S.,Sharapa, Dmitriy I.,Levandovsky, Igor A.,Serafin, Michael,Fokin, Andrey A.,Rodionov, Vladimir N.
, p. 2144 - 2150 (2013)
The rearrangement of easily accessible Cookson's diketone with chlorosulfonic acid in chloroform followed by the acidic hydrolysis gave 6-chloro-7-hydroxy-dichloropentacyclo[6.3.0.02,6.0 3,10.05,9]undecane-4-one, whose syn-stereochemistry was assigned through the X-ray crystal structure analysis. This key structure was used for the stereoselective synthesis of the D 3-trishomocubane derivatives as well as for the preparation of potential drugs bearing hydroxy- and amino-functional groups. A new multigram preparative synthesis of D 3-trishomocubane was developed.
The first cns-active carborane: A novel p2x7 receptor antagonist with antidepressant activity
Wilkinson, Shane M.,Gunosewoyo, Hendra,Barron, Melissa L.,Boucher, Aurelie,McDonnell, Michelle,Turner, Peter,Morrison, Daniel E.,Bennett, Maxwell R.,McGregor, Iain S.,Rendina, Louis M.,Kassiou, Michael
, p. 335 - 339 (2014/06/09)
Relative to other polycyclic frameworks (1-3), a carborane cage (4 and Cs·5) exerts a significant biological effect as an inhibitor of the purinergic P2X7 receptor (P2X7R) which allows one to target depression in vivo and thus demonstrate, for the first time, that a carborane has the capacity to modify CNS activity.
Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists
Sklyarova, Anna S.,Rodionov, Vladimir N.,Parsons, Christopher G.,Quack, Guenter,Schreiner, Peter R.,Fokin, Andrey A.
, p. 360 - 366 (2013/03/29)
Computational modeling demonstrates that the van-der-Waals surfaces of homocubyl amines are similar to that of the neuroprotector Memantine . Utilizing readily available precursors we report the preparation of a series of homological cubylamines, namely pentacyclo[6.3.0. 02,6.03,10.05,9]undecyl-4-amine (trishomocubyl-4-amine, 2), pentacyclo[5.3.0.02,5.0 3,9.04,8]decyl-10-amine (bishomocubyl-10-amine, 3), pentacyclo[4.3.0.02,5.03,8.04,7]nonyl-9-amine (homocubyl-9-amine, 4), and pentacyclo[4.2.0.02,5.0 3,8.04,7]octyl-1-amine (cubylamine, 5). The hydrochlorides of amines 2-5 show pronounced affinity for the (+)MK-801 channel binding site, and it seems likely that these compounds would act as very fast voltage-dependent NMDA receptor antagonists.
Novel polycyclic 'cage'-1,2-diamines as potential anti-tuberculosis agents
Onajole, Oluseye K.,Coovadia, Yacoob,Kruger, Hendrik G.,Maguire, Glenn E.M.,Pillay, Melendhran,Govender, Thavendran
, p. 1 - 9 (2012/09/08)
A series of polycyclic 'cage' derivatives of N-geranyl-1,2 diamines were synthesized and screened for their anti-mycobacterial activity against H 37Rv, multidrug resistant (MDR) and extensively drug-resistant (XDR) strains of tuberculosis. By substituting the adamantyl skeleton of SQ109 with trishomocubanyl (9), oxa-pentacycloundecyl (14, 16), pentacycloundecyl, PCU, (10, 15) and azapentacycloundecyl (22, 23), the effect of other polycyclic "cage" skeletons could be investigated. Compound 9 (trishomocubanyl moiety) proved to be the most active (MICs: 0.5-2 μg/mL) while PCU hydroxyl derivatives (15 and 23), oxa-pentacycloundecyl and azapentacycloundecyl derivatives displayed similar activity to SQ109 (MICs: 0.5-4 μg/mL) against all three strains of TB used in this study.
D3-trishomocubane-4-carboxylic acid as a new chiral building block: Synthesis and absolute configuration
Gaidai, Alexandr V.,Volochnyuk, Dmitriy M.,Shishkin, Oleg V.,Fokin, Andrey A.,Levandovskiy, Igor A.,Shubina, Tatyana E.
, p. 810 - 816 (2012/05/07)
The preparation of (±)-D3-trishomocubanone on a multigram scale from 1,4-benzoquinone and cyclopentadiene was optimized to give the target product in 39% overall yield, that was transformed to (±)-D 3-trishomocubane-4-carboxylic acid via a three-step procedure involving the Corey-Chaykovsky reaction followed by boron trifluoride-diethyl ether catalyzed epoxide ring opening and further oxidation. Optically active (+)-D3-trishomocubane-4-carboxylic acid was prepared through the resolution of the racemate by crystallization of its salt with (R)-phenylethylamine; the absolute configuration was assigned by X-ray crystal structure analysis. Georg Thieme Verlag Stuttgart · New York.
REACTIONS OF TETRACYCLO4,11.05,9>UNDECANE-2,7-DIONE WITH ELECTROPHILIC HALOGENATING REAGENTS
Petrenko, A. E.,Aleksandrov, A. M.,Sorochinskii, A. E.,Kukhar, V. P.
, p. 2038 - 2041 (2007/10/02)
The reaction of tetracyclo4,11.05,9>undecan-2,7-dione with boron tribromide leads to the formation of derivatives of pentacyclo3,6.02,10.05,9>undecane.In the reactions with phosphorus pentachloride and sulfur tetrafluoride the main products are 1,7-dichloro- and 1,7-difluoro-12-oxapentacyclo2,6.03.10.05.9>undecanes.
Carbonylation and Valence Isomerization of 1,3-Dihomocubane Derivatives by Chlorodicarbonylrhodium Dimer
Zlotogorski, Changa,Blum, Jochanan,Osawa, Eiji,Schwartz, Helmut,Hoehne, Gerhard
, p. 971 - 976 (2007/10/02)
1,3-Dihomocubane and several analogous cage compounds react with Rh2(CO)4Cl2 to give dinuclear acyl-rhodium complexes.These complexes are transformed into dicyclopentadiene and/or D3-trihomocubanone derivatives either upon heating or by treatment with triphenylphosphine. 1,3-Ethanomethanocubane reacts analogously.The kinetics of these metal-induced transformations follow the second-order rate law.A linear relationship exists between the constants and the calculated strain energies of the starting cage compounds.
